Supplementary Materials for. Kinetic and Computational Studies on Pd(I) Dimer- Mediated Halogen Exchange of Aryl Iodides
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- Χθόνιος Κορωναίος
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1 Supplementary Materials for Kinetic and Computational Studies on Pd(I) Dimer- Mediated Halogen Exchange of Aryl Iodides Indrek Kalvet, a Karl J. Bonney, a and Franziska Schoenebeck a * a Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, Aachen, Germany franziska.schoenebeck@rwth-aachen.de Contents: ps2-4 ps6-28 ps29-33 ps34 Kinetic data; Computational data; NMR spectra of used compounds; References. ps1
2 Kinetic Data Scheme S1. Halogen exchange between [(PtBu3P)PdBr]2 (1) and 5. Aryl Iodide 7 Study 7,0 0,12 [ArBr] mm 6,0 5,0 4,0 3,0 2,0 1,0 0, t (min) 41 mm [ArI] 82 mm [ArI] 123 mm [ArI] 158 mm [ArI] 200 mm [ArI] d[arbr]/dt (mm/min) 0,10 0,08 0,06 R² = 0,9976 0,04 0,02 0,00 0,00 0,10 0,20 [ArI](M) Figure S1. Rate of formation of 6 with different initial concentrations of 5 (quantified by integration of the proton at 6.68 ppm against the CH2 resonance of the internal standard at 3.82 ppm). Table S1. R 2 values, demonstrating the fit of the data to the applied linear trendlines in Figure S1, and values for the gradient of the trendline for each [ArI]0. [ArI]0(mM) R 2 d[arbr]/dt (mm/min) ps2
3 [(PtBu3P)PdBr]2 (1) Study 3,0 [ArBr] (mm) 2,5 2,0 1,5 1,0 0,5 0, t (min) [1] (mm) Figure S2. Rate of formation of 6 with different initial concentrations of 1. d[arbr]/dt (mm/min) 0,08 0,07 0,06 0,05 0,04 0,03 0,02 0,01 0,00 R² = 0, [1](mM) Table S2. R 2 values, demonstrating the fit of the data to the applied linear trendlines in Figure S2, and values for the gradient of the trendline for each [1]0. [1]0(mM) R 2 d[arbr]/dt (mm/min) ps3
4 Activation Barrier Study A [ArBr] mm 3,5 3,0 2,5 2,0 1,5 1,0 0,5 0, Figure S3. A - Formation of 6 at different temperatures. B - logarithm of [1] vs time at different temperatures. t (min) t( o C) B ln([1]) -4,55-4,65-4,75-4,85-4,95 t (min) t( o C) rate*10 6 1,4 1,2 1,0 0,8 0,6 0,4 0,2 0, t ( o C) Figure S4. Rate of consumption of 1 at different temperatures. Table S3. R 2 values, demonstrating the fit of the data to the applied linear trendlines in Figure S3-B, and absolute values for the gradient of the trendline for each temperature. t ( o C) R 2 gradient ps4
5 Computational data Computational Methods. All calculations were performed with the Gaussian 09 program package.1 Structural optimizations and frequency calculations were performed with B3LYP and ωb97xd functionals along with 6-31G(d) basis set on lighter atoms and the ECP LanL2DZ on Pd and I atoms. Single point energy calculations were performed with alternative DFT methods and G(d,p) basis set on lighter and Stuttgart-Dresden ECP on Pd and I atoms (BS1) or def2-tzvp on all atoms (BS2). Benzene solvation was taken into account using the CPCM solvation model. Frequency analysis was used to confirm whether the structure is a minima (NImag = 0) or a transition state (NImag = 1). Intrinsic reaction coordinate (IRC) analysis was used to confirm that the obtained transition states connect the correct minima. D3-corrections have been calculated using the Becke-Johnson damping function. 2 All energies were corrected to 1M standard state.3 Data from ωb97xd optimized structures Figure S5. Free energy pathway of the halogen exchange reaction between Br-dimer 1 and 1- iodo-2-methoxynaphthalene 5, calculated at CPCM (benzene) M06L/def2TZVP //ωb97xd/6-31g(d) [with LANL2DZ for Pd,I]. Values are reported in kcal/mol. Table S4. Comparison of experimentally obtained activation free energy barrier with calculated activation free energies. Different solvation corrected (CPCM=benzene) single point energies were calculated with G(d,p) basis set and SDD ECP (BS1) or def2tzvp (BS2) on //ωb97xd/6-31g(d)[with LANL2DZ for Pd,I] optimized geometries. All values are reported in kcal/mol and are relative to the starting materials 1 and 5. Method TS-1 (Ox. Add.) G TS-2 (Red. Elim.) Experiment 24.9± 3.3 M06L/BS M06L/BS M06-2X/BS M06-2X/BS ωb97xd/bs ωb97xd/bs B3LYP/BS B3LYP/BS BP86/BS BP86/BS B3LYP-D3/BS B3LYP-D3/BS BP86-D3/BS BP86-D3/BS ps5
6 XYZ and thermal data 1 Pd Br P C C C Br Pd P C C C C H H H C H H H C H H H C H H H C H H H C H H H C H H H C H H H C H H H C H H H C H H H C H H H C H H H C ps6
7 H H H C H H H C H H H C H H H C H H H B3LYP optimization Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= CPCM (Benzene) M06L/def2-TZVP E = CPCM (Benzene) M062X/def2TZVP E = CPCM (Benzene) BP86/def2TZVP E = CPCM (Benzene) B3LYP/def2TZVP E = CPCM (Benzene) wb97xd/def2tzvp E = CPCM (Benzene) M06L/ G(d,p) with SDD (for Pd) E = CPCM (Benzene) M062X/ G(d,p) with SDD (for Pd) E = CPCM (Benzene) BP86/ G(d,p) with SDD (for Pd) E = CPCM (Benzene) wb97xd/ g(d,p) with SDD (for Pd) E = CPCM (Benzene) B3LYP/ G(d,p) with SDD (for Pd) E = BP86-D3 correction = B3LYP-D3 correction = ωb97xd optimization (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= CPCM (Benzene) M06L/def2TZVP E = CPCM (Benzene) M062X/def2TZVP E = CPCM (Benzene) wb97xd/def2tzvp E = CPCM (Benzene) BP86/def2TZVP E = CPCM (Benzene) B3LYP/def2TZVP E = CPCM (Benzene) M06L/ G(d,p) with SDD (for Pd) E = CPCM (Benzene) M062X/ G(d,p) with SDD (for Pd) E = CPCM (Benzene) wb97xd/ g(d,p) with SDD (for Pd) E = CPCM (Benzene) BP86/ G(d,p) with SDD (for Pd) E = CPCM (Benzene) B3LYP/ G(d,p) with SDD (for Pd) E = BP86-D3 correction = B3LYP-D3 correction = ps7
8 Ox. Add. TS-1 C C C C C C Pd Pd Br H H C C H H P C C C C H H H H H H C C C C C C H H H H H H H H H H H H H H H H H H P C C C C C C C C C C C C H H H H ps8
9 H H H H H H H H H H H H H H H H H H H H H H H C C H H C C H H H O C H H H I Br B3LYP optimization (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= CPCM (Benzene) M06L/def2TZVP E = CPCM (Benzene) M062X/def2TZVP E = CPCM (Benzene) BP86/def2TZVP E = CPCM (Benzene) B3LYP/def2TZVP E = CPCM (Benzene) wb97xd/def2tzvp E = CPCM (Benzene) M06L/ G(d,p) with SDD (for Pd, I) E = CPCM (Benzene) M062X/ G(d,p) with SDD (for Pd, I) E = CPCM (Benzene) BP86/ G(d,p) with SDD (for Pd, I) E = CPCM (Benzene) wb97xd/ g(d,p) with SDD (for Pd, I) E = CPCM (Benzene) B3LYP/ G(d,p) with SDD (for Pd, I) E = BP86-D3 correction = B3LYP-D3 correction = ωb97xd optimization (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= CPCM (Benzene) M06L/def2TZVP E = CPCM (Benzene) M062X/def2TZVP E = ps9
10 CPCM (Benzene) wb97xd/def2tzvp E = CPCM (Benzene) BP86/def2TZVP E = CPCM (Benzene) B3LYP/def2TZVP E = CPCM (Benzene) M06L/ G(d,p) with SDD (for Pd, I) E = CPCM (Benzene) M062X/ G(d,p) with SDD (for Pd, I) E = CPCM (Benzene) wb97xd/ g(d,p) with SDD (for Pd, I) E = CPCM (Benzene) BP86/ G(d,p) with SDD (for Pd, I) E = CPCM (Benzene) B3LYP/ G(d,p) with SDD (for Pd, I) E = BP86-D3 correction = B3LYP-D3 correction = C C C C C C Pd Pd Br H H C C H H P C C C C H H H H H H C C C C C C H H H H H H H H H H H H H H H H H H P C C C C ps10
11 C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H C C H H C C H H H O C H H H I Br B3LYP optimization (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= CPCM (Benzene) M06L/def2-TZVP E = ωb97xd optimization (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= CPCM (Benzene) M06L/def2-TZVP E = ps11
12 C C C C C C Pd Pd Br H H C C H H P C C C C H H H H H H C C C C C C H H H H H H H H H H H H H H H H H H P C C C C C C C C C C C C H H ps12
13 H H H H H H H H H H H H H H H H H H H H H H H H H C C H H C C H H H O C H H H Br I B3LYP optimization (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= CPCM (Benzene) M06L/def2-TZVP E = ωb97xd optimization (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= CPCM (Benzene) M06L/def2-TZVP E = ps13
14 Red. Elim. TS-2 C C C C C C Pd Pd Br H H C C H H P C C C C H H H H H H C C C C C C H H H H H H H H H H H H H H H H H H P C C C C C C C C C C C C H H ps14
15 H H H H H H H H H H H H H H H H H H H H H H H H H C C H H C C H H H O C H H H Br I B3LYP optimization (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= CPCM (Benzene) M06L/def2TZVP E = CPCM (Benzene) M062X/def2TZVP E = CPCM (Benzene) BP86/def2TZVP E = CPCM (Benzene) B3LYP/def2TZVP E = CPCM (Benzene) wb97xd/def2tzvp E = CPCM (Benzene) M06L/ G(d,p) with SDD (for Pd, I) E = CPCM (Benzene) M062X/ G(d,p) with SDD (for Pd, I) E = CPCM (Benzene) BP86/ G(d,p) with SDD (for Pd, I) E = CPCM (Benzene) wb97xd/ g(d,p) with SDD (for Pd, I) E = CPCM (Benzene) B3LYP/ G(d,p) with SDD (for Pd, I) E = BP86-D3 correction = B3LYP-D3 correction = ωb97xd optimization (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= ps15
16 CPCM (Benzene) M06L/def2TZVP E = CPCM (Benzene) M062X/def2TZVP E = CPCM (Benzene) wb97xd/def2tzvp E = CPCM (Benzene) BP86/def2TZVP E = CPCM (Benzene) B3LYP/def2TZVP E = CPCM (Benzene) M06L/ G(d,p) with SDD (for Pd, I) E = CPCM (Benzene) M062X/ G(d,p) with SDD (for Pd, I) E = CPCM (Benzene) wb97xd/ g(d,p) with SDD (for Pd, I) E = CPCM (Benzene) BP86/ G(d,p) with SDD (for Pd, I) E = CPCM (Benzene) B3LYP/ G(d,p) with SDD (for Pd, I) E = BP86-D3 correction = B3LYP-D3 correction = Pd P C C C Br Pd P C C C C H H H C H H H C H H H C H H H C H H H C H H H C H H H C H H H C H H H C H H H C H H H ps16
17 C H H H C H H H C H H H C H H H C H H H C H H H C H H H I B3LYP optimization (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= CPCM (Benzene) M06L/def2-TZVP E = ωb97xd optimization (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= CPCM (Benzene) M06L/def2-TZVP E = Ox. Add. TS-3 C C C C C C Pd Pd Br H H ps17
18 C C H H P C C C C H H H H H H C C C C C C H H H H H H H H H H H H H H H H H H P C C C C C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H ps18
19 H H H C C H H C C H H H O C H H H I I B3LYP optimization (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= CPCM (Benzene) M06L/def2-TZVP E = ωb97xd optimization (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= CPCM (Benzene) M06L/def2-TZVP E = C C C C C C Pd Pd I H H C C H H P C C C C ps19
20 H H H H H H C C C C C C H H H H H H H H H H H H H H H H H H P C C C C C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H C C H H C C ps20
21 H H H O C H H H I Br B3LYP optimization (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= CPCM (Benzene) M06L/def2-TZVP E = ωb97xd optimization (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= CPCM (Benzene) M06L/def2-TZVP E = I4 C C C C C C Pd Pd I H H C C H H P C C C C H H H H H H C C C C C C H ps21
22 H H H H H H H H H H H H H H H H H P C C C C C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H C C H H C C H H H O C H H H Br I ps22
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